Chester Rentals

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355 Houses

Amazing Maine Get-Away - Maine's Western Mountains

Andover house

  • 16 bedrooms
  • 7 bathrooms
  • sleeps 32

Match: Private outdoor pool (unheated) Cycling trips

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Price per night from

$1,145

Resort Home with Hot Tub Pools Fireplace

Campton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 13 minutes

Match: Private outdoor pool (unheated) Cycling trips

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Price per night from

$287

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The Little Red House with Prize Ocean View

Rockport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$196

Sand Mirage Beach Home - PEI's North Shore, Savage Harbour

Savage Harbour cottage

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$164

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (unheated), Cycling trips

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Price per night from

$493

1 of 2 match: Private outdoor pool (unheated), Cycling trips

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Price per night from

$344

Summer Tranquility in Cape Cod

Eastham studio

  • Studio
  • 1 bathroom
  • sleeps 2

“Great place!” Amazing and comfortable small cottage! Everything you needed is there so you don't have to worry about anything. It's close to the highway, but the trees and bushes are hiding it so you don't realy see it! Would recommend it!

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$115

Exciting, spacious, vacation condo

Provincetown condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great location” I love this condo, the location is fantastic and it comes with all the comforts of home. This was my second year and I plan on booking next summer.

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$164

Ocean View Condo across from Beach with pool!

Dennis Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 26 minutes

1 of 2 match: Private outdoor pool (unheated), Cycling trips

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Price per night from

$172

Cozy Wells cottage close to beach-avail 6/28-7/5

Wells cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 46 minutes

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$217

92 Locust Lane

North Conway house

  • 16 bedrooms
  • 11 bathrooms
  • sleeps 34

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$2,977

80 Locust Lane

North Conway house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$1,203

42 Locust Lane

North Conway house

  • 10 bedrooms
  • 5 bathrooms
  • sleeps 20

1 of 2 match: Private outdoor pool (unheated), Cycling trips

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Price per night from

$1,947

70 Locust Lane

North Conway house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$1,054

Responds fast! avg. 1 hour 52 minutes

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$361

Ocean Front Cottage on Penobscot Bay

Belfast cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$321

Cape Cod 2 Bedroom Cottage 100 yards to the Beach

Dennis Port cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Beach cottage on beautiful Cape Cod” We had a lovely visit at the Glendon cottage #99. Cape Cod has so much to offer, we went exploring everyday, from the beautiful sunrise to sunset. The seafood from the area was outstanding. We could hear the waves crashing against the shore, with the beach just a short walk away. The cottage was nicely equipped, and decorated with beach and nautical themes. in pastel colors, we found pleasant to the eye. We found the furniture uncomfortable for sitting, at the dining table, and the sofa for watching T.V. The bathroom toilet was too low and difficult for us to get on/off of. We would have brought a clock, coffee pot, a bathmat, and picked up a local map, had we known we would need them. GPS is poor at the Cape. Also, information r/t garbage recycling, pick-up etc. and list of local T.V. stations would have helped out. Putting all this aside, we enjoyed our stay at the beach.

Responds fast! avg. 1 hour 21 minutes

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$315

Edgartown - Clean, quiet, and comfortable home close to bike trail

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$745

Waterfront Home on Scenic Cove

Harpswell house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$184

Cozy Cottage Near the Beaches in Newport, RI!!

Middletown house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$544

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$237

Wild Pines Cabins

Belfast cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$101

Victoria Cottage Garden Suite

Victoria house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful accommodation” My partner and I stayed at this location for four nights, and loved it. This is a self-contained efficiency apartment, with everything convenient and well planned. The kitchen is fully equipped and easy to use. This is a bright, cheerful place, very clean, and welcoming. The views from the windows look out over farmers' fields. It was delightful and we were reluctant to leave. We would definitely recommend it to anyone, and will come back when we are in PEI. We are cyclists and found that Victoria is a good place to cycle out and back from. The rides are easy and scenic along the coast. Cycling inland is challenging, but the roads are quiet and drivers very friendly. Jeanne and Susan are wonderful hosts and gave us fresh beans and onions from their garden.

Responds fast! avg. 3 hours 3 minutes

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$109

Modern Luxe Loft

Needham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$172

Lieutenant Island Treehouse Getaway

Wellfleet house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 39 minutes

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$1,543

Private Contemporary Cape Set on a Hilltop

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$344

Relaxing Eco-Friendly Home Next to Long Pond Beach

Harwich house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$218

The Land Yacht: A spectacular Oceanfront Estate With Indoor Pool!

Hubbards house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$669

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$687

Steps to Campground Road Beach! A/C, Wifi, Outdoor Shower, Grill

Eastham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Great Location! Great Time!” We were so happy to find this rental. The cottage is a gem...well maintained and nicely decorated with a cute beachy theme. It's in a great setting that provided nice privacy and some shade from the summer sun. Love the outdoor shower! The cottage is located so near to the beach that the kids were able to walk there safely by themselves. The owners were very professional to work with and the transaction went seamlessly. We look forward to returning in 2012!

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$659

10 Locust Lane

North Conway house

  • 15 bedrooms
  • 9 bathrooms
  • sleeps 32

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$2,748

Luxury Kennebunkport Cottage w/ Private Water Access

Cape Porpoise house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 minutes

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$401

Salt Water Farm,The Studio, Waterfront Organic

Brooksville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$170

Sea Glenn Flowers Private home new to market

Vineyard Haven house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$481

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$228

Idyllic Suite, Ocean and Island Views near Acadia

Southwest Harbor apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$162

Riverside Cottage

Bonshaw cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Would recommend to anyone with no hesitation - excellent vacation in PEI” Every day spent in Bonshaw was excellent. Hiking trails are wonderful. River closeby for canoeing and kayaking. Such a beautiful place to enjoy nature. The owners were warm and welcoming and the cottage was beautiful and very very clean. Cozy cottage with view of nature. Close to everything, especially beautiful beaches. If we have the opportunity, we would love to go again!

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$118

Haiku House - your gateway to Acadia

Acadia National Park cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Cycling trips

1 of 2 filters match

Price per night from

$544

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